The 1999 MTV Video Music Awards, held on September 9, 1999, at the Metropolitan Opera House in New York City, was a night filled with memorable performances, unexpected moments, and significant wins. Hosted by Chris Rock, the ceremony honored the best music videos released between June 13, 1998, and June 11, 1999. This particular event stood out not only for its celebration of musical artistry but also for several incidents that captured public attention
and contributed to its lasting legacy in VMA history.
Lauryn Hill's Historic Wins and Hip-Hop's Recognition
Lauryn Hill emerged as the night's biggest winner, taking home four awards. Her critically acclaimed video for "Doo Wop (That Thing)" secured the prestigious Video of the Year award, marking a historic moment as it was the first hip-hop video to achieve this honor. This win underscored a growing recognition of hip-hop's influence and artistic merit within the mainstream music industry. Hill's success highlighted a shift in the landscape of popular music, demonstrating the genre's ability to resonate with a broad audience and earn top accolades.
Beyond her individual triumph, the ceremony also saw other significant artists recognized. Ricky Martin, for instance, won two competitive awards for his hit "Livin’ la Vida Loca," specifically Best Pop Video and Best Dance Video. He also received three International Viewer's Choice Awards, further cementing his global appeal. Other notable winners included Korn, TLC, and Eminem, showcasing the diverse range of musical talent celebrated that evening.
Controversial Outfits and Calls for Peace
The 1999 VMAs were not without their share of controversy and impactful statements. One of the most talked-about moments involved Diana Ross and Lil' Kim. Lil' Kim's outfit, which left her entire left breast exposed save for a small pastie on her nipple, drew considerable attention. During the ceremony, Diana Ross famously jiggled Lil' Kim's exposed breast, an impromptu action that became an iconic, if controversial, highlight of the night. This moment sparked discussions about fashion, celebrity, and public display.
In a more somber and significant moment, the mothers of slain rappers Tupac Shakur and The Notorious B.I.G., Afeni Shakur and Voletta Wallace, appeared together to present the Best Rap Video Award. Their joint presence on stage was a powerful symbol of unity and remembrance, transcending the rivalries that had once defined their sons' careers. Additionally, Adam Horovitz of the Beastie Boys used his platform to make a plea for peace, specifically addressing the sexual assaults that had occurred at Woodstock '99, bringing a serious social issue to the forefront of the awards show.
Tributes, Debuts, and Uninvited Guests
The ceremony also featured a tribute to Madonna, who held the record as the most-nominated artist in VMA history. This tribute involved a host of male drag performers dressed as the iconic singer, recreating her looks from past music videos, celebrating her enduring impact on the industry. The night also served as a platform for emerging pop sensations. Britney Spears made her VMA debut, performing her breakout single "...Baby One More Time," while NSYNC also performed their song "Tearin' Up My Heart," showcasing the rising stars of the teen pop era.
An unexpected incident occurred when the Backstreet Boys accepted their award for Viewer's Choice. A stranger, later identified as John Del Signore, crashed the stage and cryptically stated, "Wake up at 3." It was later revealed that Del Signore's intention was a failed attempt to sell a show idea to Viacom. This bizarre interlude added another layer of unpredictability to an already eventful night. The awards show also leveraged cross-promotions, notably with SEGA, as the date coincided with the launch of their Dreamcast game console, intertwining music and gaming culture.
